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    City: Chestertown, MD
    Listing Status: Active
    Map
    122 Properties Available In Chestertown

    122 Properties Available In Chestertown

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    • Beds (Most)
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    MD >Chestertown >
    Market Insights
    201 RIVER RD, Chestertown, MD 21620
    1/44
    Open Sat 1:30PM-3:30PM

    $629,900

    3 Beds2 Baths2,430 SqFt

    201 RIVER RD, Chestertown, MD 21620

    MLS# MDQA2017684

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    101 S MILL ST, Chestertown, MD 21620
    1/39
    Open Sat 11AM-1PM

    $515,000

    2 Beds3 Baths1,476 SqFt

    101 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006674

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    104 CONLEY DR, Chestertown, MD 21620
    1/27
    Open 6/19 11AM-1PM

    $247,000

    3 Beds2 Baths1,280 SqFt

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686

    Listed by Cummings & Co. Realtors

    Bright MLS (BMLS)
    103 TRAFFORD DR, Chestertown, MD 21620
    1/65
    Open Sat 11AM-1PM

    $399,900

    3 Beds3 Baths1,944 SqFt

    103 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    7989 QUAKER NECK RD, Chestertown, MD 21620
    1/90
    Open Sat 11AM-1PM
    3D

    $2,200,000

    5 Beds5 Baths4,305 SqFt

    7989 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    517 ROUND TOP RD, Chestertown, MD 21620
    1/28
    New

    $349,900

    3 Beds1 Bath1,248 SqFt

    517 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2017680

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    202 ROYSTON SHORES RD, Chestertown, MD 21620
    1/72
    New

    $1,200,000

    4 Beds3 Baths2,292 SqFt

    202 ROYSTON SHORES RD, Chestertown, MD 21620

    MLS# MDQA2017462

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    104 ACORN DR, Chestertown, MD 21620
    1/26
    New

    $284,900

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    234 N COLLEGE AVE, Chestertown, MD 21620
    1/3
    Price Dropped by $20K

    $100,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    8796 MARYLAND PKWY, Chestertown, MD 21620
    1/60
    Active

    $1,650,000

    9 Beds7 Baths4,776 SqFt

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    110 PROSPECT ST, Chestertown, MD 21620
    1/6
    Active

    $119,895

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
    1904 PONDTOWN RD, Chestertown, MD 21620
    1/11
    Active

    $265,000

    3 Beds1 Bath1,967 SqFt

    1904 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2017480

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    10781 FERMOY RD, Chestertown, MD 21620
    1/54
    Active

    $449,900

    4 Beds3 Baths2,160 SqFt

    10781 FERMOY RD, Chestertown, MD 21620

    MLS# MDKE2006640

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    213 BYFORD DR, Chestertown, MD 21620
    1/39
    Active

    $380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    21172 WYOMING AVE, Chestertown, MD 21620
    Active

    $200,000

    4 Beds1 Bath2,920 SqFt

    21172 WYOMING AVE, Chestertown, MD 21620

    MLS# MDKE2006642

    Listed by Blue Star Real Estate, LLC

    Bright MLS (BMLS)
    22470 FAIRGALE FARM LN, Chestertown, MD 21620
    1/49
    Active

    $1,450,000

    4 Beds5 Baths4,257 SqFt

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    Price Dropped by $25K

    $425,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    956 WASHINGTON AVE, Chestertown, MD 21620
    1/29
    Active

    $285,000

    3 Beds1 Bath1,248 SqFt

    956 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006394

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    102 FLYING CLOUD DR, Chestertown, MD 21620
    1/41
    Active

    $339,900

    3 Beds3 Baths1,896 SqFt

    102 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006586

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    240 MERGANSER DR, Chestertown, MD 21620
    1/51
    Price Dropped by $10K
    3D

    $389,000

    3 Beds2 Baths1,120 SqFt

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    107 FLYING CLOUD DR, Chestertown, MD 21620
    1/51
    Price Dropped by $10K

    $385,000

    5 Beds4 Baths2,534 SqFt

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510

    Listed by CENTURY 21 New Millennium

    Bright MLS (BMLS)
    304 HADAWAY DR, Chestertown, MD 21620
    1/38
    Price Dropped by $7K
    3D

    $314,900

    4 Beds2 Baths1,325 SqFt

    304 HADAWAY DR, Chestertown, MD 21620

    MLS# MDKE2006482

    Listed by Redfin Corporation

    Bright MLS (BMLS)
    214 SILVER HEEL RD, Chestertown, MD 21620
    1/26
    Price Dropped by $10K

    $340,000

    4 Beds3 Baths1,972 SqFt

    214 SILVER HEEL RD, Chestertown, MD 21620

    MLS# MDKE2006498

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    407 HIGH ST, Chestertown, MD 21620
    1/57
    Price Dropped by $30K

    $798,000

    3 Beds5 Baths3,047 SqFt

    407 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
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    explore listings in Chestertown

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    AMB Property Group | Keller Williams Capital Properties
    Angelica Dennis
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    +1(240) 688-8762
    angelica@ambpropertygroup.com
    519 C Street NE, Washington, DC, 20002

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    AMB (1)
    AMB Property Group | Keller Williams Capital Properties
    Angelica Dennis
        Top Areas
        1. Prince Georges County
        2. Montgomery County
        3. Anne Arundel County
        4. Calvert County
        5. Charles County
        6. Washington, DC
        7. Northern Virginia
        Buyers
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        Sellers
        1. Home Valuation
        2. Sell My Home
        3. Services
        4. Schedule
        Market Snapshot
        News
        About Us
    +1(240) 688-8762
    angelica@ambpropertygroup.com
    519 C Street NE, Washington, DC, 20002

    Get My App

    Do Not Sell or Share My Personal Data
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.